As I rubbed the head of my cock against my sister-in-law's puckered asshole I felt the extreme rush of what I was doing course through me. I was going to do it. Finally I was going to fulfill my deepest, darkest, most secret desire.
Sarah, my sister in law, moaned unintelligibly. I held her there, pinned against the side of the pool, her bikini bottom floating around her ankles next to my own swimming trunks as I grinded against her exposed ass.
She had been hanging onto the edge, peeking outwards when she'd passed out. I had quickly moved into position behind her before she could hurt herself and now held her against the edge, one hand on her small left breast, which I squeezed gleefully through the small leopard- print bikini top while I held her in place with my other hand around her and wedged firmly in her crotch, fingering the folds of her pussy, exploring the hidden warmth of her cunt. My cock, as I had previously stated, was pressing hard against her asshole.
She was resting her head on her arms, which were up on the edge of the pool, and even though she was out of it, her body was responding to my attentions. I could see her eyes were half closed and staring out into space, a little bit of drool was dripping from her lip onto her forearm, but even in that state the juices that were flowing from her pussy warmed my fingers as they probed inside her.
She was making small little grunts as my cock, which I had smeared up with Vaseline in the hopes that it would do as lube in the pool, slowly pushed its head through her relaxing sphincter, until it popped fully into her anal cavity.
It was so exciting that I thought I could have cum right then and there, but just like I tried to get a hold of myself at that moment, let's not get ahead of ourselves in the story. After all, a great cock- tease like my sister-in-law deserves a thorough, slow fucking, so I'll try to go slow as I recount the events that led me to this point.
I'm just a regular guy, working as a writer after years of frustrating attempts at other careers- mostly in the tech industry- left me hating that world of business and stress and deadlines, trading it in for the role of 'house-husband' if you will, which gave me time to work on my writing, but also gave the seeds of dark desire that twisted within me a chance to set out roots and grow.
Average height, average build, nothing much spectacular about me, although I've been told I have a nice smile. Nothing spectacular to say regarding my cock either, not going to embellish and say that I have a huge dong when I'm actually pretty average. A respectable 5-inch-er that served me well enough while I was single, and was more than enough for my wife.
Now, about my wife. You might think that since I'm in the process of nailing her sister that she's rather 'meh', but far from it. She's actually quite the looker, beautiful face and a metabolically thin body that helped her shed the pounds after having kids so that she still has the body of a slim twenty-year-old. Dark, shoulder length hair against creamy skin, and a tramp stamp on her lower back from when she was younger actually makes her pretty damn hot, and I love fucking her.
That's not the issue.
The problem was that my wife was a prude. The tattoo was something she did to try to prove to herself that she could be wild, that she had a bad side, but in the end, she's about as dark and wild as mid-afternoon tea. When we fuck, which is regularly, thank god, we have a routine that we've followed for the past ten years of marriage. I get on top of her missionary style, then I turn her around for doggy, and then if she hasn't cum yet, she gets on top for a go, but usually what happens is that she cums before that.
That's it. Two or three times a week, that ain't bad, straight- up fucking. I usually finger her afterwards for a second orgasm; sometimes I finger her before as foreplay, which is actually better because after cumming from my finger on her clit, when I give her my immensely average cock, she does go a little wild, panting and moaning a lot and giving me a good run for my money in holding out until she comes a second time.
Like I said, my wife is great, I love her to death and wouldn't trade the life we have for anything. But... there's just something inside me. Something that hungers for more. Something that wants some forbidden fruit.
Now, I've been with my wife for the better part of thirteen years. We met in college and graduated together, even worked on our thesis together. we were the picture-perfect couple. Married after college, waited until we were stable financially to have our first kid, and three years later added the second one.
During all that time, I've never cheated on her. I've had plenty of chances to. It's funny how having a ring on your finger can turn an average guy into slut-bait. There was no shortage of office tramps in the places I worked in after graduating, and I even came close once, on a business trip, but I backed out at the last minute. Like I said, I didn't want to ruin what I had.
My sister-in-law, however, had been unwittingly undermining my resolve for the better part of a decade.
She is my wife's older sister by a couple of years, and she is lust incarnate. At least for me. I don't know what it is about her. She's not particularly hotter than my wife. She's shorter, has smaller tits and her personality is nowhere near as endearing. In fact, she's kind of a bitch. Still, there's something about that raven-haired cock- tease that wouldn't leave my brain, once she got in.
I blame pornography.
Being in a 'vanilla-sex' relationship, I was and still am an avid porn browser. I have over 100 Gigabytes of porn in my hard drive, all categorized by actress, which I use to indulge myself on whatever whimsy takes me on any particular day, sometimes even after my wife has fallen asleep, exhausted after our plain fucking.
Because for better or worse, those fucking sluts know what guys like. They suck cock. They give up the ass. They talk dirty. They ask for you to cum for them, on them, in them. They look into the camera, right as they take a huge load on their face, in their mouth, on their tits, and give you a devilish smile as they lap up the cum streaked across their face, dribbling out of their mouths. They fuck in cars, showers, changing rooms, offices, on desks, merry-go-rounds and in pools. God bless porn stars!
Now, when I say I blame pornography, I don't really mean that I necessarily believe that shit about how it warps your brain, except that in my case, I think it's true!
I've been obsessed with fucking my sister-in-law for the past five years or so, all because of what I stumbled upon one night browsing the internet for the latest young talent. I was browsing my favorite porn site when I saw a thumbnail of a slim, dark-haired little slut choking on a huge cock. I could have sworn on a bible, at that moment, that it was my sister-in-law.
Still, once I opened up the picture gallery, the resemblance was striking. She had the same exotic look. The smoky eyes. The long, dark hair that reached half-way to her back. Legs that seemed to go on forever, a hot, smooth and tight ass that begged to be fucked. Her tits were on the smallish size, barely a handful, but all that did was remind me more of Sarah. A small waist that accentuated her silhouette in the pictures where she was bending over, taking it from behind.
I was transfixed.
I immediately beat myself off and made a more than usual mess of the sheets while my wife snored next to me. I pulled up a picture of a trip to the beach and put the pictures of both of them side-by-side. They could have been sisters. Damn. It was honestly the first time I had ever thought of my sister-in-law in that way. I mean, I'd always thought she was pretty, but her personality was so off-putting that nothing sexual had ever occurred to me.
Now there I was, covered in cum-soiled blankets, holding my dick, which was still hard, looking at a couple of pictures, one of Sarah, the other one of some hot whore who was enjoying a deep fucking who looked just like her. Did I mention that I was still hard? I immediately jacked off a second time, but when I came, I was no longer looking at the porn star's picture. I was looking at my sister-in-law.
Something happened then. My brain made some connection, some synapse misfired or something, because from that moment on, my sister- in-law became the foremost object of my obsessions.
In the following weeks I downloaded all the videos I could find of that porn star. Aside from having a shrill voice that wasn't at all like Sarah's husky, throaty one, the more videos I watched, the more she became my sister-in-law.
I browsed though gigabyte after gigabyte of family pictures in my computer, copying those where Sarah appeared and placing them in a hidden folder. Cutting everyone else from the pictures until I had a huge gallery of jpgs where she was in bathing suits, in parties, even at her wedding.
Fuck, she was hot. Now, with my obsessed brain working overtime, I couldn't see how I hadn't noticed it before. She's fucking gorgeous. I especially loved the pictures I had of some of her birthdays, where she's got her luscious lips puckered as she's blowing out the candles, except that now, in my mind, it's my cock that she's blowing. Even though I have a lot of pictures, I want more. I need more.
One of the annoyances of having a career in IT had always been that you automatically became Tech Support for you family. Am I right? Now, finally there was a chance to turn that all around. I was able to get a jump start to my new super-creep, stalker persona, because luckily, Sarah and her husband weren't particularly computer savvy. I had just been at their place a few months earlier to clean up their computer and update their anti-virus as a favor in the middle of a family reunion at their place.
Her husband was a doctor. She wasn't exactly a trophy wife, she had a lucrative career too as a corporate lawyer, so they had a pretty big place in a good neighborhood in town, with a large pool in the back-yard. Most of the birthdays and family reunions were celebrated there because of it. The didn't have any kids yet.
In any case, my point is that I knew I would have a shot at what I wanted, eventually. Their files. I HAD to find more pictures. Of course, at this point in the tale, I hadn't really thought that I would ever get a chance to fuck her, I just wanted more wanking material.
By the time I finally got my chance, about six months into my obsession, I had memorized every picture I had of her. I had beat my meat raw every night looking at her pictures on one side of the screen while keeping a small window with a video of her doppelganger porn star on the other side of the screen.
When I got the chance, at one of my kids' birthdays, I casually told her husband if he wanted me to take a look at their computer. He was so grateful! He led me to their home office and left me there, alone, with the only computer in their house.
I immediately removed a 1.5 TB external drive from my pocket and plugged it into the laptop. I didn't know how much time I would have, so I just copied the entire hard drive. I gave a cursory glance at the antivirus software I had installed previously, which was running perfectly. I cleaned the computer registry and sat back to wait. It was all I could do not to open their document files and start looking for pictures. I reminded myself to be patient.
The transfer was around 80% when Sarah walked into the room. Now, if you remember I told you I had always found her to be kind of a bitch, but being accustomed to working with assholes most of my professional life, I'm actually a damn good hypocrite. This, and the fact that my wife was always deferential to her big sister, and was very close to her, had made it so that I had always adopted a friendly attitude with her, despite her bitchiness.
Of course, now I could reap in the rewards of that. Sarah had always seen me as a nice guy, a stand-up guy, and basically not a threat. So over the years, she had probably grown used to feeling safe around me, even when she was wearing bathing suits, like she was at that very moment.
She didn't know it, but things had changed between us. As she came into the room, I was glad I hadn't been looking through their files, since that would certainly have meant that I would have had a raging hard-on. When she entered, catching me off guard, it was the first time I know for a fact that she saw the hunger in my eyes. I was very cautious after that.
She was standing there in a yellow bikini that left little to the imagination. Her body was fucking tight and toned. Even though she had smallish tits, they were perfect for her body. Her hips and stomach were fucking awesome, and I just wanted to lick the entire length of her legs as she stood there.
Like I said, the hunger must have shown for a moment, because whatever she had been about to say died on her lips as she met my eyes, and she actually gave a small step backwards.
Realizing my eyes had been roaming her entire body, the skin she was showing, I quickly played it off as if I was making an exaggerated joke, leering and ogling her openly and bugging my eyes at her, telling her it was a kid's party, not a modeling audition.
The suspicion faded from her eyes as she remembered who she was talking to, and she laughed and gave me a little playful jiggle. I could have died at that moment, but I continued playing the part of the harmless jokester.
"Oh yeah, give us a turn!" I called to her, and she started giggling, her perky breasts bounced as she did a complete turn and shook her bottom at me.
I shifted down in my seat immediately before she could notice that my cock was hardening. Still playing, I told her:
"Oh, good thing I'm sitting down so you don't see my erection!"
She laughed again, her body quivering and came to stand by me. she punched me softly on the arm and told me how silly I was.
"How much of a mess have we made with the computer now?"
Completely aware of her bare stomach just inches from my face as she stood next to me I fought every fiber of my being not to lean over and lick her belly button. I showed her the virus scan report.
"Oh just cleaning the registry and cookies so your browser runs faster. You should really stop using internet explorer."
It was all Greek to her, and she shook her head, saying as much.
"OK pointdexter, just hurry up, your daughter wants everyone in the pool."
I watched her ass sway from side to side as she walked away, the edge of the bikini slightly wedged between her plump cheeks and at that very moment I knew I was lost. I knew, that if I EVER got the chance, I would fuck her brains out.
I finished the file transfer and tucked away the hard drive in my pocket for my later audit.
Time passed, and we actually moved away for a while. My wife got a great job offer at another city on the other side of the country, so we packed up our stuff and moved. I spent a good six months looking for a job, but the economy was still reeling and there were too many jobless workers in the tech industry.
In that time, I made a good accounting of myself taking care of the kids and maintaining the house, so my wife, who as I said is awesome, encouraged me to take the time to work on my dream, which was to be a writer. She was making enough that we were in a decent place financially, and the time with me at home was doing wonders for our kids, who were developing into polite, smart and funny little persons that were the center of our existence. So I became a stay-at-home dad that tried to write when he had the chance.
Of course, there was a huge obstacle to my efforts at concentrating when I was alone and the kids were at school.
All the files I had plundered from Sarah's computer were in a zipped, password-protected folder on my personal laptop, categorized by now in folders such as 'bathing suit', 'face', 'body', 'wedding' and my favorite, 'Greatest Hits' which was where I copied the best shots where my sister-in-law's poses obliged my fantasies and made her look like the slut I wanted her to be.
Sadly for me, the non-tech couple didn't have any secret sex- tapes, or naked pictures for me to find, but I still had her porn star lookalike to help me with that.
For the next couple of years the status quo remained. I continued gathering pictures from social media sites where my sister- in-law posted her photos. One Christmas, when we visited, I installed an on-line backup service on their laptop, one for which I kept an access code to, so that I could continue to sack and pillage their document files, keeping myself up to date.
When I wasn't jerking off to pictures of Sarah, or imagining I was fucking her while I was inside my wife, I actually got some writing done. I sold a manuscript for a sci-fi novel and began gathering a small but growing fan-base that after a couple of years actually made me feel like a real author. I wasn't exactly breaking into the best sellers lists, but my following novels began to appear in bookstores and I began to make enough money that I convinced my wife to move back home.
Luckily, she was homesick as well, and missing our families, so she took a less lucrative, but still decent job back in our home town and we bought a house right in my sister-in-law's neighborhood. We could afford it now.
During the months of planning our move back, my ulterior motives were constantly jumping to the forefront of my mind. I was going to be close to Sarah again. My obsession, which had cooled down some being so geographically distant, had started to consume me. All I saw was her face and her body when I went to sleep, when I fucked my wife, whenever I closed my eyes.
The porn star lookalike had gotten a huge boob job in that time that totally ruined the illusion for me, even though it made her much more popular as an actress. She was no longer the spitting image of my sister-in-law, so I kept watching her old videos when I needed to simulate fucking Sarah's sweet mouth. Her tight ass. I imagined cumming all over her gorgeous face as she pleaded for more.
I had to find a way. It was an itch that just wouldn't quit until it was scratched.
When we finally moved back and had our housewarming party, Sarah came with her goofball husband, and I saw that she was still as fuckeable as ever.
The face that had launched a thousand wanks smiled delightedly when she saw me. You see, now that I was a semi-famous author, my stock had gone up. She hugged me tightly and I had to turn to one side to try and hide my hard-on.
She peppered me with questions about my books, how I came up with the stories, and seemed particularly interested in how I came up with the steamy details of the sex scenes I wrote for my characters.
"God, you guys must have a pretty hot sex-life." I heard her comment to my wife, whose prudishness in all fairness had softened when she'd begun to read my stuff.
Yes sir, my wife had begun sucking my cock on a fairly regular basis, after years together where it was a maybe-two-times-a-year thing and only on my birthday and our anniversary, and I admit that while a lot of the times in my mind it was her sister who was sucking me off, sometimes her own face would remain, her own lips wrapped around my cock as she tried to take more of it in.
It was something new for her, and I appreciated it very much, since I had always been a fan of getting my dick sucked. Who isn't right? It was tough going, at first, she had a small mouth and even my average-sized cock filled it up easily. She had hesitancy issues at first, because she stopped every time she scraped her teeth around my shaft, which hurt, true, but she paused to make sure I was okay every time, so it was slow going.